Diisopropylethylamine → benzyl 5-[(N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

HRID 2395107Notes

Reaction equation

HRID 2395107 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26].[CH:41]1[C:53]2[CH:52]([CH2:54][O:55][C:56]([NH:58][C@@H:59]([C:68](O)=[O:69])CC(OC(C)(C)C)=O)=[O:57])[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]=2[CH:44]=[CH:43][CH:42]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=C[CH:83]=[CH:84][C:79]=2N=N1.[CH:93](N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH:50]1[C:51]2[CH:52]([CH2:54][O:55][C:56]([NH:58][C@@H:59]([C:68]([NH:8][CH2:9][C:10]3[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]4[C:11]=3[O:12][C:13]3[C:14]([CH2:30][C:31]([O:33][CH2:34][C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=3[C:19]4([CH3:27])[CH3:26])=[O:69])[CH2:2][C:3](=[O:4])[O:5][C:84]([CH3:83])([CH3:79])[CH3:93])=[O:57])[C:53]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:46]=2[CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70188164-tert-Butyl N-((9H-Fluoren-9-ylmethoxy)carbonyl)-D-aspartateHCID 18972493Benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate

Product 1

HCID 86753151benzyl 5-[(N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.17 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate and 0.14 g of N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid in 5 ml of dimethylformamide was treated, with 0.11 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate and with 0.11 ml of diisopropylethylamine. The mixture was stirred at room temperature for 1 hour and thereafter poured into dilute sodium bicarbonate solution. The resulting precipitate was filtered off, washed with water KHSO4 /K2SO4 solution and again with water and dried with 40° in a vacuum, whereby 0.25 g of benzyl 5-[(N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained; MS: 841.5 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with water KHSO4 /K2SO4 solution and again with water
  3. customdried with 40° in a vacuum

Sources & evidence

ORD record
ord-55ce479f8a1841c99e69e03efa2856ca
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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